NPASS Compound

Structure

NPC43971 OpenBabel07101719512D 29 33 0 0 1 0 0 0 0 0999 V2000 2.2272 -1.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 -1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6065 1.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7405 0.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6065 2.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8744 1.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7405 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4103 4.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5443 3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0084 3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8963 -0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8744 2.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2764 3.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1424 4.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5443 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0084 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4103 2.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2764 2.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 -1.1977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1424 5.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5873 -0.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1424 2.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1988 1.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 24 2 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 25 2 0 0 0 0 16 18 2 0 0 0 0 16 28 1 0 0 0 0 17 27 1 0 0 0 0 18 20 1 0 0 0 0 19 18 1 1 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 26 1 6 0 0 0 22 28 1 1 0 0 0 22 29 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.13
Volume:	392.595
LogP:	4.827
LogD:	3.194
LogS:	-4.905
# Rotatable Bonds:	3
TPSA:	74.97
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	3.773
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.691
MDCK Permeability:	6.73990580253303e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	87.55621337890625%
Volume Distribution (VD):	1.44
Pgp-substrate:	9.41201114654541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.276
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.429
CYP2C19-substrate:	0.143
CYP2C9-inhibitor:	0.574
CYP2C9-substrate:	0.375
CYP2D6-inhibitor:	0.351
CYP2D6-substrate:	0.336
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	2.157
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.897
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.71
Rat Oral Acute Toxicity:	0.291
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.211
Carcinogencity:	0.517
Eye Corrosion:	0.003
Eye Irritation:	0.041
Respiratory Toxicity:	0.22

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC43971

Natural Product ID:	NPC43971
*Common Name:**	XTIQPKJOGKMOSY-ILWGZMRPSA-N
IUPAC Name:	n.a.
Synonyms:	(-)-Semiglabrin
Standard InCHIKey:	XTIQPKJOGKMOSY-ILWGZMRPSA-N
Standard InCHI:	InChI=1S/C23H20O6/c1-12(24)26-21-19-18-16(28-22(19)29-23(21,2)3)10-9-14-15(25)11-17(27-20(14)18)13-7-5-4-6-8-13/h4-11,19,21-22H,1-3H3/t19-,21-,22+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@H]2[C@@H](OC1(C)C)Oc1c2c2oc(cc(=O)c2cc1)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL377111
PubChem CID:	11741220
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16644212]
NPO16665	Tephrosia semiglabra	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2089123]
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO626	Indigofera tinctoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16665	Tephrosia semiglabra	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	7

Activity Type	# Activity
NON-MOLECULAR	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	36.0	%	PMID[550420]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	25.0	%	PMID[550420]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	13.0	%	PMID[550420]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	8.0	%	PMID[550420]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	19.0	%	PMID[550420]
NPT2632	Organism	Syrian golden hamster	Mesocricetus auratus	Activity	=	60.0	%	PMID[550420]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	70.0	%	PMID[550421]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC43971 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	437
0.1-0.2	1692
0.2-0.3	3429
0.3-0.4	8459
0.4-0.5	10618
0.5-0.6	4577
0.6-0.7	5941
0.7-0.8	6210
0.8-0.85	1198
0.85-0.9	127
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC19554
1.0	High Similarity	NPC74749
0.9803	High Similarity	NPC50430
0.9551	High Similarity	NPC91288
0.9416	High Similarity	NPC470625
0.9304	High Similarity	NPC471286
0.9057	High Similarity	NPC34376
0.9026	High Similarity	NPC164299
0.9013	High Similarity	NPC294365
0.9013	High Similarity	NPC171656
0.9	High Similarity	NPC93215
0.9	High Similarity	NPC310603
0.8938	High Similarity	NPC92589
0.8931	High Similarity	NPC43761
0.8931	High Similarity	NPC113055
0.8924	High Similarity	NPC475797
0.8924	High Similarity	NPC469936
0.8924	High Similarity	NPC155063
0.8924	High Similarity	NPC211482
0.8924	High Similarity	NPC474609
0.8924	High Similarity	NPC109967
0.8924	High Similarity	NPC129053
0.8924	High Similarity	NPC474738
0.8924	High Similarity	NPC17521
0.8924	High Similarity	NPC321372
0.8924	High Similarity	NPC78554
0.8924	High Similarity	NPC476652
0.891	High Similarity	NPC318424
0.8868	High Similarity	NPC310206
0.8861	High Similarity	NPC108937
0.8861	High Similarity	NPC279218
0.8854	High Similarity	NPC31627
0.8854	High Similarity	NPC68882
0.8854	High Similarity	NPC476238
0.8854	High Similarity	NPC327269
0.8812	High Similarity	NPC470607
0.8805	High Similarity	NPC45165
0.879	High Similarity	NPC471675
0.879	High Similarity	NPC290671
0.879	High Similarity	NPC470380
0.8765	High Similarity	NPC302741
0.8765	High Similarity	NPC18284
0.8765	High Similarity	NPC273021
0.875	High Similarity	NPC23817
0.875	High Similarity	NPC470856
0.875	High Similarity	NPC43638
0.875	High Similarity	NPC470606
0.8742	High Similarity	NPC469934
0.8734	High Similarity	NPC285623
0.8734	High Similarity	NPC473996
0.8726	High Similarity	NPC180351
0.8726	High Similarity	NPC472421
0.8718	High Similarity	NPC168085
0.8712	High Similarity	NPC183672
0.8704	High Similarity	NPC94155
0.8696	High Similarity	NPC73511
0.869	High Similarity	NPC325176
0.8688	High Similarity	NPC149368
0.8688	High Similarity	NPC265480
0.8688	High Similarity	NPC127406
0.8684	High Similarity	NPC136095
0.8684	High Similarity	NPC473209
0.8684	High Similarity	NPC11566
0.8683	High Similarity	NPC72455
0.8679	High Similarity	NPC168805
0.8679	High Similarity	NPC121910
0.8679	High Similarity	NPC131725
0.8675	High Similarity	NPC76047
0.8675	High Similarity	NPC120220
0.8671	High Similarity	NPC472636
0.8671	High Similarity	NPC472580
0.8671	High Similarity	NPC474772
0.8671	High Similarity	NPC23253
0.8671	High Similarity	NPC474744
0.8671	High Similarity	NPC472423
0.8667	High Similarity	NPC320789
0.8662	High Similarity	NPC317492
0.8659	High Similarity	NPC294722
0.8659	High Similarity	NPC72016
0.8655	High Similarity	NPC106700
0.8654	High Similarity	NPC243154
0.8654	High Similarity	NPC282335
0.8654	High Similarity	NPC218300
0.8654	High Similarity	NPC473428
0.865	High Similarity	NPC44947
0.865	High Similarity	NPC125991
0.865	High Similarity	NPC131745
0.865	High Similarity	NPC478199
0.8642	High Similarity	NPC200708
0.8642	High Similarity	NPC472320
0.8642	High Similarity	NPC271479
0.8634	High Similarity	NPC117478
0.8634	High Similarity	NPC161749
0.8634	High Similarity	NPC258644
0.8634	High Similarity	NPC197896
0.8634	High Similarity	NPC258035
0.8634	High Similarity	NPC313163
0.8634	High Similarity	NPC156457
0.8634	High Similarity	NPC122809
0.8627	High Similarity	NPC472409
0.8625	High Similarity	NPC295608
0.8625	High Similarity	NPC470604
0.8625	High Similarity	NPC278010
0.8625	High Similarity	NPC470605
0.8625	High Similarity	NPC99233
0.8625	High Similarity	NPC284353
0.8625	High Similarity	NPC478238
0.8625	High Similarity	NPC250769
0.8625	High Similarity	NPC470603
0.8623	High Similarity	NPC223375
0.8623	High Similarity	NPC472584
0.8623	High Similarity	NPC475825
0.8618	High Similarity	NPC36414
0.8616	High Similarity	NPC288534
0.8616	High Similarity	NPC477957
0.8616	High Similarity	NPC256141
0.8616	High Similarity	NPC40033
0.8614	High Similarity	NPC477165
0.8614	High Similarity	NPC41853
0.8614	High Similarity	NPC473202
0.8609	High Similarity	NPC254741
0.8609	High Similarity	NPC161196
0.8608	High Similarity	NPC476185
0.8608	High Similarity	NPC474735
0.8608	High Similarity	NPC191104
0.8608	High Similarity	NPC321896
0.8598	High Similarity	NPC124155
0.8598	High Similarity	NPC179198
0.8598	High Similarity	NPC257566
0.8598	High Similarity	NPC278419
0.8598	High Similarity	NPC66087
0.8589	High Similarity	NPC303913
0.8589	High Similarity	NPC47923
0.8589	High Similarity	NPC97812
0.8589	High Similarity	NPC14822
0.8589	High Similarity	NPC175513
0.8581	High Similarity	NPC59522
0.8581	High Similarity	NPC17262
0.858	High Similarity	NPC311574
0.858	High Similarity	NPC308265
0.858	High Similarity	NPC104677
0.858	High Similarity	NPC264932
0.858	High Similarity	NPC40583
0.8571	High Similarity	NPC98776
0.8571	High Similarity	NPC301897
0.8562	High Similarity	NPC106625
0.8562	High Similarity	NPC478213
0.8562	High Similarity	NPC472583
0.8562	High Similarity	NPC7989
0.8562	High Similarity	NPC78021
0.8562	High Similarity	NPC87304
0.8562	High Similarity	NPC223701
0.8562	High Similarity	NPC268950
0.8562	High Similarity	NPC279930
0.8562	High Similarity	NPC472515
0.8562	High Similarity	NPC108706
0.8562	High Similarity	NPC211158
0.8555	High Similarity	NPC294863
0.8555	High Similarity	NPC282636
0.8554	High Similarity	NPC476459
0.8554	High Similarity	NPC167479
0.8553	High Similarity	NPC253616
0.8553	High Similarity	NPC259685
0.8553	High Similarity	NPC471676
0.8553	High Similarity	NPC472420
0.8553	High Similarity	NPC471291
0.8553	High Similarity	NPC103001
0.8553	High Similarity	NPC472422
0.8553	High Similarity	NPC263384
0.8553	High Similarity	NPC244577
0.8545	High Similarity	NPC475979
0.8544	High Similarity	NPC104236
0.8544	High Similarity	NPC88445
0.8544	High Similarity	NPC164205
0.8537	High Similarity	NPC259834
0.8537	High Similarity	NPC150164
0.8537	High Similarity	NPC414831
0.8535	High Similarity	NPC471285
0.8535	High Similarity	NPC14875
0.8528	High Similarity	NPC95472
0.8528	High Similarity	NPC328102
0.8528	High Similarity	NPC321478
0.8528	High Similarity	NPC303210
0.8528	High Similarity	NPC172687
0.8528	High Similarity	NPC239270
0.8528	High Similarity	NPC298093
0.8528	High Similarity	NPC49009
0.8528	High Similarity	NPC306978
0.8526	High Similarity	NPC179970
0.8526	High Similarity	NPC469953
0.8521	High Similarity	NPC66804
0.8519	High Similarity	NPC19097
0.8519	High Similarity	NPC161650
0.8519	High Similarity	NPC210048
0.8519	High Similarity	NPC288084
0.8516	High Similarity	NPC147145
0.8512	High Similarity	NPC235575
0.8509	High Similarity	NPC27408
0.8509	High Similarity	NPC95090
0.8509	High Similarity	NPC470681

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC43971 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	889
0.2-0.3	1713
0.3-0.4	2701
0.4-0.5	2062
0.5-0.6	984
0.6-0.7	281
0.7-0.8	132
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8634	High Similarity	NPD4381	Clinical (unspecified phase)
0.8609	High Similarity	NPD2796	Approved
0.8562	High Similarity	NPD7096	Clinical (unspecified phase)
0.8528	High Similarity	NPD5494	Approved
0.85	High Similarity	NPD6801	Discontinued
0.8443	Intermediate Similarity	NPD3818	Discontinued
0.8418	Intermediate Similarity	NPD920	Approved
0.8405	Intermediate Similarity	NPD7075	Discontinued
0.8393	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD6559	Discontinued
0.8344	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD7819	Suspended
0.8323	Intermediate Similarity	NPD1243	Approved
0.8291	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6599	Discontinued
0.8261	Intermediate Similarity	NPD4380	Phase 2
0.821	Intermediate Similarity	NPD7411	Suspended
0.8187	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3817	Phase 2
0.8133	Intermediate Similarity	NPD919	Approved
0.811	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7054	Approved
0.8065	Intermediate Similarity	NPD3748	Approved
0.8063	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1549	Phase 2
0.8023	Intermediate Similarity	NPD7074	Phase 3
0.8023	Intermediate Similarity	NPD7472	Approved
0.7989	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6797	Phase 2
0.7963	Intermediate Similarity	NPD5403	Approved
0.7962	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD5401	Approved
0.7949	Intermediate Similarity	NPD1510	Phase 2
0.7939	Intermediate Similarity	NPD1934	Approved
0.7931	Intermediate Similarity	NPD7251	Discontinued
0.7904	Intermediate Similarity	NPD7768	Phase 2
0.7895	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7808	Phase 3
0.7862	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3749	Approved
0.7844	Intermediate Similarity	NPD5402	Approved
0.7834	Intermediate Similarity	NPD2799	Discontinued
0.7824	Intermediate Similarity	NPD1247	Approved
0.7824	Intermediate Similarity	NPD7199	Phase 2
0.7812	Intermediate Similarity	NPD3750	Approved
0.7798	Intermediate Similarity	NPD4966	Approved
0.7798	Intermediate Similarity	NPD4965	Approved
0.7798	Intermediate Similarity	NPD4967	Phase 2
0.7798	Intermediate Similarity	NPD3882	Suspended
0.7784	Intermediate Similarity	NPD2801	Approved
0.7759	Intermediate Similarity	NPD5844	Phase 1
0.7758	Intermediate Similarity	NPD7458	Discontinued
0.7756	Intermediate Similarity	NPD1933	Approved
0.7746	Intermediate Similarity	NPD7473	Discontinued
0.7735	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2534	Approved
0.773	Intermediate Similarity	NPD2532	Approved
0.773	Intermediate Similarity	NPD2533	Approved
0.7706	Intermediate Similarity	NPD6234	Discontinued
0.7702	Intermediate Similarity	NPD4628	Phase 3
0.7702	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1240	Approved
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2313	Discontinued
0.7674	Intermediate Similarity	NPD6232	Discontinued
0.7669	Intermediate Similarity	NPD1511	Approved
0.7662	Intermediate Similarity	NPD6832	Phase 2
0.7647	Intermediate Similarity	NPD2798	Approved
0.764	Intermediate Similarity	NPD2800	Approved
0.764	Intermediate Similarity	NPD8313	Approved
0.764	Intermediate Similarity	NPD8312	Approved
0.763	Intermediate Similarity	NPD3926	Phase 2
0.7619	Intermediate Similarity	NPD37	Approved
0.7616	Intermediate Similarity	NPD6959	Discontinued
0.7595	Intermediate Similarity	NPD1607	Approved
0.7586	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6166	Phase 2
0.7584	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1512	Approved
0.7574	Intermediate Similarity	NPD8455	Phase 2
0.7562	Intermediate Similarity	NPD2935	Discontinued
0.7562	Intermediate Similarity	NPD1551	Phase 2
0.7561	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7487	Intermediate Similarity	NPD7584	Approved
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7468	Intermediate Similarity	NPD3267	Approved
0.7468	Intermediate Similarity	NPD3266	Approved
0.7459	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7286	Phase 2
0.744	Intermediate Similarity	NPD3226	Approved
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD8434	Phase 2
0.7407	Intermediate Similarity	NPD2346	Discontinued
0.7407	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2403	Approved
0.7386	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7229	Phase 3
0.7358	Intermediate Similarity	NPD4307	Phase 2
0.7342	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD7685	Pre-registration
0.7333	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD3887	Approved
0.733	Intermediate Similarity	NPD7435	Discontinued
0.7312	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5124	Phase 1
0.7312	Intermediate Similarity	NPD6355	Discontinued
0.7306	Intermediate Similarity	NPD7583	Approved
0.7303	Intermediate Similarity	NPD3751	Discontinued
0.7301	Intermediate Similarity	NPD2344	Approved
0.7299	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5006	Approved
0.7277	Intermediate Similarity	NPD5005	Approved
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3787	Discontinued
0.7273	Intermediate Similarity	NPD6808	Phase 2
0.7268	Intermediate Similarity	NPD7585	Approved
0.7263	Intermediate Similarity	NPD6777	Approved
0.7263	Intermediate Similarity	NPD6781	Approved
0.7263	Intermediate Similarity	NPD6779	Approved
0.7263	Intermediate Similarity	NPD6776	Approved
0.7263	Intermediate Similarity	NPD6778	Approved
0.7263	Intermediate Similarity	NPD6780	Approved
0.7263	Intermediate Similarity	NPD6782	Approved
0.7251	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5890	Approved
0.7251	Intermediate Similarity	NPD5889	Approved
0.7244	Intermediate Similarity	NPD2797	Approved
0.7243	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD8151	Discontinued
0.7212	Intermediate Similarity	NPD2654	Approved
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1019	Discontinued
0.7195	Intermediate Similarity	NPD6004	Phase 3
0.7195	Intermediate Similarity	NPD6002	Phase 3
0.7195	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6005	Phase 3
0.7195	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6585	Discontinued
0.719	Intermediate Similarity	NPD17	Approved
0.7181	Intermediate Similarity	NPD4360	Phase 2
0.7181	Intermediate Similarity	NPD4363	Phase 3
0.7178	Intermediate Similarity	NPD4308	Phase 3
0.7176	Intermediate Similarity	NPD1653	Approved
0.7175	Intermediate Similarity	NPD5711	Approved
0.7175	Intermediate Similarity	NPD5710	Approved
0.7168	Intermediate Similarity	NPD1465	Phase 2
0.716	Intermediate Similarity	NPD6651	Approved
0.7158	Intermediate Similarity	NPD4420	Approved
0.7157	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7783	Phase 2
0.715	Intermediate Similarity	NPD7696	Phase 3
0.715	Intermediate Similarity	NPD7698	Approved
0.715	Intermediate Similarity	NPD7697	Approved
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7136	Intermediate Similarity	NPD7930	Approved
0.7135	Intermediate Similarity	NPD5242	Approved
0.7135	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1203	Approved
0.7126	Intermediate Similarity	NPD2309	Approved
0.7126	Intermediate Similarity	NPD4288	Approved
0.7125	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1296	Phase 2
0.7125	Intermediate Similarity	NPD6798	Discontinued
0.7113	Intermediate Similarity	NPD7871	Phase 2
0.7113	Intermediate Similarity	NPD7870	Phase 2
0.7107	Intermediate Similarity	NPD7874	Approved
0.7107	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2353	Approved
0.7091	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1471	Phase 3
0.7069	Intermediate Similarity	NPD5760	Phase 2
0.7069	Intermediate Similarity	NPD5761	Phase 2
0.7059	Intermediate Similarity	NPD6273	Approved
0.7051	Intermediate Similarity	NPD9717	Approved
0.7051	Intermediate Similarity	NPD3972	Approved
0.7051	Intermediate Similarity	NPD1608	Approved
0.7031	Intermediate Similarity	NPD8285	Discontinued
0.703	Intermediate Similarity	NPD6100	Approved
0.703	Intermediate Similarity	NPD2438	Suspended
0.703	Intermediate Similarity	NPD6099	Approved
0.7029	Intermediate Similarity	NPD5353	Approved
0.7026	Intermediate Similarity	NPD8320	Phase 1
0.7026	Intermediate Similarity	NPD8319	Approved
0.7019	Intermediate Similarity	NPD3764	Approved
0.7017	Intermediate Similarity	NPD7799	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data